Kelly Osbourne's Dating History: Two Failed Engagements To Baby With Friend Of 23 Years, Sid Wilson

You might recognise Kelly Osbourne for her stint in reality television. For those unversed, she has starred in the MTV show, The Osbournes, and with a background in fashion, she has also hosted Fashion Police and Project Catwalk. Her acting credits include CSI: Cyber, So Undercover, and The Muppets' Wizard of Oz, among others.  

While Kelly often finds herself in the headlines for her variety of works, this time, however, it's a little different. The 41-year-old recently sparked social media chatter about her dramatic weight loss. Her sudden transformation comes months after her father, Ozzy Osbourne's death. As someone whose moves never go unnoticed, Kelly's dating life has also been in the spotlight on more than one occasion. In case you, too, are interested in learning about all of her romantic relationships, here's everything we know.  

Kelly Osbourne and Bert McCracken's on-and-off relationship  

If you have followed the Osbournes' family show closely, you might have seen how Kelly Osbourne's relationship with The Used's Bert McCracken played out. Appearing in the second season of the reality show, the duo's relationship is best described as on-and-off. In an interview with Playboy, Bert revealed that in the end, he broke up with Kelly in one of the most terrible ways possible. If you guessed over the phone, you are absolutely right. Apparently, he wasn't ready for the type of relationship that Kelly wanted, and that, between the two, he was the bigger problem. However, he did admit in a conversation with Metro that Kelly was a very important girlfriend to him, stating: 

"She's the most important girlfriend I've ever had. We're best friends. It was always just so pleasant when she was around."  

Kelly Osbourne's relationship with Danny Jones possibly ended because of her dad  

Kelly once again fell for a musician following her split with her ex-boyfriend, Bert McCracken. This time, it was none other than Danny Jones, whom she dated in 2008. Initially, it seemed their relationship was headed in a good direction, but later, as it turns out, Kelly's father might have been the reason she put the brakes on it. During an interview with The Mirror in 2008, Danny recalled a night when they were still together. He revealed that Kelly took him to her family home in Buckinghamshire after a night out.

According to him, he initially decided to stay the night at Kelly's home. While the couple was sitting downstairs and chatting, Ozzy Osbourne showed up, made some awkward small talk, and eventually left the room. In the end, Danny opted to leave for the night, as not being able to properly introduce himself to Ozzy was something that “didn't feel right” to him. After this interaction, he apparently never heard back from her again.  

Kelly Osbourne's relationship with Luke Worrall ended on bad terms 

Kelly's next relationship was far longer than her previous ones. After her breakup with Danny Jones, she dated model, Luke Worrall, who was five years her junior. The two did not end their relationship on good terms, as the fashion designer accused him of cheating on her at the end of their relationship. Both Kelly and Luke turned to social media to vent out their frustrations after the breakup.  

Kelly Osbourne moved on with Rob Damiani 

Kelly took a break from dating for about a year after ending things badly with Luke Worrall. After being ready to enter a relationship once again, she dated musician, Rob Damiani. Not much is known about their relationship, as this time around, Kelly decided to focus and keep things pretty private. One thing we do know, however, is that Kelly moved on with Rob. In the end, once again, things didn't work out for the duo, and Kelly found herself single again. In March 2011, she told The Mirror:

"I don't have a boyfriend right now. What's wrong with people? I stand next to a man and I'm with them. It's boring"

Kelly Osbourne was engaged to Matthew Mosshart 

Kelly Osbourne got engaged to chef, Matthew Mosshart in January 2013. According to her, she and her fiancé were incredibly close, so much so that many people thought that they had a co-dependent relationship. They even started planning their wedding, with Kelly wanting her Mom to be in charge of the whole event. However, a year later, they called off their engagement, only stating that their split was amicable and nothing more.  

Kelly Osbourne dated model, Ricki Hall for a short while 

A few months after Kelly called off her engagement, she found herself in a brand-new relationship. This time around, she dated model, Ricki Hall. They moved in together in July 2014. Kelly even shared an intimate photo of the two embracing, leaving her fans gasping. Their relationship moving too quickly might have contributed to their eventual breakup. 

Kelly Osbourne and Sid Wilson got engaged and had a baby together

In May 2022, Kelly announced that she and Slipknot's Sid Wilson had gotten engaged. While the sudden news left some fans shocked, what was even more surprising was that she announced she was pregnant. Kelly seemed truly happy to be taking a step towards motherhood. This was evident from her Instagram post, where she wrote, “I am over the moon to announce that I am going to be a Mumma. To say that I am happy does not quite cut it. I am ecstatic!” 

The duo apparently met for the first time in 1999 but did not get into a relationship until decades later. According to a source, they met when Sid's band was touring with Ozzfest. Before getting into this serious relationship, Kelly had a couple of more flings with Erik Bragg and Jimmy Q. Currently, Sid appears to be ‘The One' for her, as Kelly herself wrote in an IG post,  "After 23 years of friendship I can't believe where we have ended up! You are my best friend, my soulmate and I am so deeply in love with you Sidney George Wilson." 

What are your thoughts on the long list of relationships that Kelly Osbourne had over the years? Let us know. 

Also read: Meet Milana Vayntrub: Actress Behind USD 500,000 Donation To LA Fire Victims, Inspired By OnlyFans?

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